He enlists the help of his butch best friend and fellow misfit, Watts ( Mary Stuart Masterson), unaware that she secretly pines for him. In a gender-reversed version of his previous hit Pretty in Pink, John Hughes retreads all-too- familiar ground in Some Kind of Wonderful, the story of a sensitive, young would-be artist, Keith ( Eric Stoltz), who vies for the affection of his high school's popularity queen, Amanda ( Lea Thompson), seemingly out of some deep-rooted insecurity regarding his social ineptitude.
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